Ketone sulfoxylate and process of making same.



UNlTED sures PATENT OFFICE AUGUST STOCK, OF HOOHST-ON-THE-MAIN, GERMANY, ASS1GNQB TO FAREWERKE VOR-M.

MEISTER LUCIUS & BRUNING, OF HfilGHST- GERMANY.

ONTHE .MAIN, GERMANY, A CORPORATIQN OF KETONE SULFOXYLATE AND PROCESS F MAKING SAME.

Specification of Letters Patent.

Patented Jail. 12, 1909.

Application filed March 6, 1906. Serial No. 304,456. (Specimen'm) compounds of the salts of sulfoxylic acid (compare Ber. d. D. (72cm. Gen. 38, 1051,

below) with ketones, may be obtained, if com-' pounds containing ketones and sulfurous acid be treated with reducing agents as long as an increase of the reducing power towards an indigo sulfonic acid solution can be ascertained.

The compounds suitable for the process are the following: 1. Ketone bisulfitcs. 2.-

Ketone sulfurous acid, that is, a solution of a ketone and of sulfurous acid in a suitable solvent. 3. Ketone hydrosulfites; they consist of ketone bisulfite and kctonesulfoxylate, analogous to the formaldehyde hydrosulfites (compare 1307'. (Z. D. Chem. Gee. 38, 1.052). As reducing agents are best suited zinc dust or iron in presence or absence of an Ill) acid.

The reaction will proceed without heating, but is accelerated at a moderately raised temperature, although temoeratures above 70 C. are'to be avoided, as otherwise the I lictonesulfoxylate is decomposed. The formation of thc ketonesulfoxylates is represented by the following formula:

Contrary to-the known formaldehyde sulfoxylates. the ketonesulfoxylates reduce a solution of indigo sulfonic acid .even in the cold; they reduce for 32 grains of the sulfur contained therein more than 131 grams of in I while sulfur dioxi'd is evolved and sulfur eliminated.

Example l -To a solution of 520 parts of sodium bisulfite of 40Ba ain in 500 parts of water are added 130 parts of acetone; 200 parts of zinc dust stirred with little water are then introduced and the inassis heated to SO- C. as long as an increase of the reducing power towards a solution of indigo sulfonic acid can be ascertained. It is then cooled, filtered and. evaporated in a vacuum. The reaction may be accelerated by adding a zinc salt, for instance, zinc chlorid. Y

Example II.-To a solution of 520 parts of sodium bisulfite of 40 B. in 500 parts of water are added 130 parts of acetone and 200 parts of iron powder. The mixture is heated to 30 (J. and at this temperature 1000 parts of dilute sulfuric acid containing 196 parts of I-I. ,SO are slowly run in. Half an hour after introducing all, acid sodium carbonate is added until the reaction is feebly alkaline and the solution of the acetone sodium sulfoxylate is filtered from the iron mud. in this example, for the sulfuric acid may be substituted the equivalent quair tity of another acid, for instance, acetic acid.

Example IIl.-To 1000 p.311 is of a solntion of zinc bisultitc, containing ll-t parts thereof are added 05 parts of acetone. 120 Parts of zinc dust. are then introduced while stirring and the whole is heated for 6 hours to 50 Sodium carbonate is then added until the reaction is fully alralinc and the solution is filtered from the separated /in carbonate. lly evaporating; in a vacuum, sodium acetone sult'oxylatc is obtained in solid form.

Example IV.--'lo 1000 par s of a solution 1 of zinc. hydrosulfite contaiuii'ig' 193 parts of $5118 0, are added 130 parts of acetonewand after the latter has reacted on the hydrosulfite the whole is heated with 120 parts of zinc dust to 50 C. for 6 hours. An addition of some zinc chlorid is of advantage. The further working up of the product of the reaction is conducted as in Example III.

Example V.-lnto a solution of parts of acetone in 1000 parts of water are intro duced 64 parts of sulfur dioxid. 120 parts of zinc dust are then added while well stirring and cooling and if no further spontaneous heating occurs the ten'lpcrature is raised to 50-60 C. After 6 hours sodium carbonate isadded and the operation conl RCO-CH .MHSO (in which R is a tinned as in Example II. In this example, monovalent hydrocarbon radical and Me is for acetone may be substituted an equivaa monovalent metal), the sodiuin-sult of v lent quantity of another ketone, for instance, which is a nearly White crystalline substance,

5 methylethylketone. soluble in cold water, and which has the 2 Having thus described my invention, I power of reducing solutions of indigo, subclaim as new and desire to secure by Letters stantially us (Inscribed.

Patent: In testimony, that I claim the foregoing l. The herein described process of makas my im'mition, I have signed my name in 10 mg ketonesulr'oxylates, Which consists in presence oi two subscribing Witnesses.

treatin" com )ounds' containin ketone and i i 7 sulfuro iis aci d-iwith reducing agents at a AUGUST 510Gb temperature below 70 C. v llituesses:

As new products, the herein described JEAN GRLIAD;

5 ketonesulfoxylates having the formula CARL Gnuzso. 

